Ergosterol_peroxide (BioDeep_00000396628)

 

Secondary id: BioDeep_00000018282, BioDeep_00000399691, BioDeep_00000621557

PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


(3S,5S,8S,9R,10R,13R,14R,17R)-17-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-5,8-epidioxycyclopenta[a]phenanthren-3-ol

化学式: C28H44O3 (428.329)
中文名称: 过氧麦角甾醇, 5Α,8Α-表二氧-(22E,24R)-麦角甾-6,22-二烯-3Β-醇
谱图信息: 最多检出来源 Viridiplantae(plant) 53.49%

分子结构信息

SMILES: C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)/C=C/[C@H](C)C(C)C)CC[C@@]4([H])[C@@]43OO[C@]2(C=C4)C[C@@H](O)C1
InChI: InChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,24+,25+,26+,27+,28-/m0/s1

描述信息

Ergosterol peroxide is an ergostanoid that is ergosta-6,22-dien-3-ol with a peroxy group between positions 5 and 8 (the 3beta,5alpha,8alpha,22E stereoisomer). Isolated from Ganoderma lucidum and Cordyceps sinensis, it exhibits antimycobacterial, trypanocidal and antineoplastic activities. It has a role as a metabolite, an antineoplastic agent, an antimycobacterial drug and a trypanocidal drug. It is an organic peroxide, an ergostanoid, a 3beta-sterol and a member of phytosterols. It is functionally related to an ergosterol.
Ergosterol peroxide is a natural product found in Benincasa hispida, Rhizoplaca melanophthalma, and other organisms with data available.
An ergostanoid that is ergosta-6,22-dien-3-ol with a peroxy group between positions 5 and 8 (the 3beta,5alpha,8alpha,22E stereoisomer). Isolated from Ganoderma lucidum and Cordyceps sinensis, it exhibits antimycobacterial, trypanocidal and antineoplastic activities.

同义名列表

40 个代谢物同义名

(3S,5S,8S,9R,10R,13R,14R,17R)-17-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-5,8-epidioxycyclopenta[a]phenanthren-3-ol; (1S,2R,5R,6R,9R,10R,13S,15S)-5-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadec-18-en-13-ol; (1S,2R,5R,6R,9R,10R,13S,15S)-5-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.01,9.02,6.010,15]nonadec-18-en-13-ol; Ergosta-6,22-dien-3-ol, 5,8-epidioxy-, (3.beta.,5.alpha.,8.alpha.,22E)-; Ergosta-6,22-dien-3-ol, 5,8-epidioxy-, (3-beta,5-alpha,8-alpha,22E)-; Ergosta-6,22-dien-3-ol, 5,8-epidioxy-, (3beta,5alpha,8alpha,22E)-; (24R)-5alpha,8alpha-epidioxy-24-methylcholesta-6,22-dien-3beta-ol; (22E,24R)-5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTA-6,22-DIEN-3.BETA.-OL; 5.ALPHA.,8.ALPHA.-EPIDOXY-(22E,24R)-ERGOSTA-6,22-DIEN-3.BETA.-OL; 5.alpha.,8.alpha.-Ergosta-6,22-dien-3.beta.-ol, 5,8-epidioxy-; (22E)-5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTA-6,22-DIEN-3.BETA.-OL; (24R)-ERGOST-5.ALPHA.,8.ALPHA.-EPIDIOXY-6,22-DIEN-3.BETA.-OL; (3beta,5alpha,8alpha,22E)-5,8-epidioxyergosta-6,22-dien-3-ol; 3.BETA.-HYDROXY-5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTA-6,22-DIENE; (22E,24R)-5alpha,8alpha-epidioxyergosta-6,22-dien-3beta-ol; Ergosta-6, 5,8-epidioxy-, (3.beta.,5.alpha.,8.alpha.,22E)-; 5-alpha,8-alpha-ERGOSTA-6,22-DIEN-3-beta-OL, 5,8-EPIDIOXY-; 5,8-Epidioxy-5-alpha,8-alpha-ergosta-6,22-dien-3-beta-ol; 5alpha,8alpha-Ergosta-6,22-dien-3beta-ol, 5,8-epidioxy-; 5alpha,8alpha-epidioxy-22E-ergosta-6,22-dien-3beta-ol; 5alpha,8alpha-Epidioxyergosta-6,22-diene-3beta-ol; 5alpha,8alpha-epidioxyergosta-6,22-dien-3beta-ol; 5-19-03-00043 (Beilstein Handbook Reference); 5.alpha.,22-dien-3.beta.-ol, 5,8-epidioxy-; 3-hydroxy-5,7-epidioxyergosta-6,22-diene; Ergosterol 5.alpha.,8.alpha.-epidioxide; Ergosterol 5-alpha,8-alpha-epidioxide; 5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTEROL; Ergosterol 5alpha,8alpha-epidioxide; 5,8-epidioxyergosta-6,22-dien-3-ol; ERGOSTEROL ENDOPEROXIDE [INCI]; ergosterol endoperoxide; ERGOSTEROL 5,8-PEROXIDE; ergosterol-5,8-peroxide; Ergosterol peroxide; ERGOSTERYL PEROXIDE; Peroxyergosterol; UNII-UG9TN81TGH; UG9TN81TGH; ST 28:3;O3



数据库引用编号

10 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

0 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表


文献列表

  • Zoha Daroodi, Parissa Taheri, Saeed Tarighi, Mehrdad Iranshahi, Maryam Akaberi. Efficacy of ergosterol peroxide obtained from the endophytic fungus Acrophialophora jodhpurensis against Rhizoctonia solani. Journal of applied microbiology. 2024 Feb; 135(2):. doi: 10.1093/jambio/lxae031. [PMID: 38346851]
  • Cong Duan, Junchi Wang, Yi Liu, Jialu Zhang, Jianyong Si, Zhihui Hao, Jiufeng Wang. Antiviral effects of ergosterol peroxide in a pig model of porcine deltacoronavirus (PDCoV) infection involves modulation of apoptosis and tight junction in the small intestine. Veterinary research. 2021 Jun; 52(1):86. doi: 10.1186/s13567-021-00955-5. [PMID: 34127062]
  • Cong Duan, Xinna Ge, Junchi Wang, Zhanyong Wei, Wen-Hai Feng, Jiufeng Wang. Ergosterol peroxide exhibits antiviral and immunomodulatory abilities against porcine deltacoronavirus (PDCoV) via suppression of NF-κB and p38/MAPK signaling pathways in vitro. International immunopharmacology. 2021 Apr; 93(?):107317. doi: 10.1016/j.intimp.2020.107317. [PMID: 33493866]
  • Chun Ru Li, Yu Qin Wang, Wen Ming Cheng, Zhu An Chen, Nigel Hywel-Jones, Zeng Zhi Li. Review on Research Progress and Prospects of Cicada Flower, Isaria cicadae (Ascomycetes). International journal of medicinal mushrooms. 2021; 23(4):81-91. doi: 10.1615/intjmedmushrooms.2021038085. [PMID: 33822510]
  • Yong-Un Jeong, Young-Jin Park. Ergosterol Peroxide from the Medicinal Mushroom Ganoderma lucidum Inhibits Differentiation and Lipid Accumulation of 3T3-L1 Adipocytes. International journal of molecular sciences. 2020 Jan; 21(2):. doi: 10.3390/ijms21020460. [PMID: 31936890]
  • Thuluz Meza-Menchaca, Irais Poblete-Naredo, Arnulfo Albores-Medina, José Pedraza-Chaverri, Francisco R Quiroz-Figueroa, Alfredo Cruz-Gregorio, Rossana C Zepeda, Guiomar Melgar-Lalanne, Irene Lagunes, Ángel Trigos. Ergosterol Peroxide Isolated from Oyster Medicinal Mushroom, Pleurotus ostreatus (Agaricomycetes), Potentially Induces Radiosensitivity in Cervical Cancer. International journal of medicinal mushrooms. 2020; 22(11):1109-1119. doi: 10.1615/intjmedmushrooms.2020036673. [PMID: 33426842]
  • Svetlana V Senik, Nadezhda V Psurtseva, Alexey L Shavarda, Ekaterina R Kotlova. Role of lipids in the thermal plasticity of basidial fungus Favolaschia manipularis. Canadian journal of microbiology. 2019 Dec; 65(12):870-879. doi: 10.1139/cjm-2019-0284. [PMID: 31398296]
  • Beixian Zhou, Xiaoli Liang, Qitong Feng, Jing Li, Xiping Pan, Peifang Xie, Zhihong Jiang, Zifeng Yang. Ergosterol peroxide suppresses influenza A virus-induced pro-inflammatory response and apoptosis by blocking RIG-I signaling. European journal of pharmacology. 2019 Oct; 860(?):172543. doi: 10.1016/j.ejphar.2019.172543. [PMID: 31323223]
  • Navneet Kishore, Pradeep Kumar, Karuna Shanker, Akhilesh Kumar Verma. Human disorders associated with inflammation and the evolving role of natural products to overcome. European journal of medicinal chemistry. 2019 Oct; 179(?):272-309. doi: 10.1016/j.ejmech.2019.06.034. [PMID: 31255927]
  • Jian Dai, Matthew A Miller, Nicholas J Everetts, Xia Wang, Peng Li, Ye Li, Jian-Hua Xu, Guang Yao. Elimination of quiescent slow-cycling cells via reducing quiescence depth by natural compounds purified from Ganoderma lucidum. Oncotarget. 2017 Feb; 8(8):13770-13781. doi: 10.18632/oncotarget.14634. [PMID: 28099150]
  • Chih-Chuang Liaw, Shu-Jing Wu, Ching-Fu Chen, Ming-Nan Lai, Lean Teik Ng. Anti-Inflammatory Activity and Bioactive Constituents of Cultivated Fruiting Bodies of Xylaria nigripes (Ascomycetes), a Chinese Medicinal Fungus. International journal of medicinal mushrooms. 2017; 19(10):915-924. doi: 10.1615/intjmedmushrooms.2017024404. [PMID: 29256845]
  • Rong Zhu, Rong Zheng, Yueyi Deng, Yiping Chen, Shuwei Zhang. Ergosterol peroxide from Cordyceps cicadae ameliorates TGF-β1-induced activation of kidney fibroblasts. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2014 Feb; 21(3):372-8. doi: 10.1016/j.phymed.2013.08.022. [PMID: 24095053]
  • Fang-Rong Chang, Chiao-Ting Yen, Mohamed El-Shazly, Cheng-Ying Yu, Ming-Hong Yen, Yuan-Bin Cheng, Shu-Li Chen, Yang-Chang Wu. Spirostanoids with 1,4-dien-3-one or 3β,7α-diol-5,6-ene moieties from Solanum violaceum. Bioorganic & medicinal chemistry letters. 2013 May; 23(9):2738-42. doi: 10.1016/j.bmcl.2013.02.060. [PMID: 23511021]
  • Shu-Jing Wu, Tzy-Ming Lu, Min-Nan Lai, Lean-Teik Ng. Immunomodulatory activities of medicinal mushroom Grifola frondosa extract and its bioactive constituent. The American journal of Chinese medicine. 2013; 41(1):131-44. doi: 10.1142/s0192415x13500109. [PMID: 23336512]
  • Hector Henrique Ferreira Koolen, Elzalina Ribeiro Soares, Felipe Moura Araújo da Silva, Antonia Queiroz Lima de Souza, Lívia Soman de Medeiros, Edson Rodrigues Filho, Richardson Alves de Almeida, Ismael Alexandre Ribeiro, Cláudia do Ó Pessoa, Manoel Odorico de Morais, Patrícia Marçal da Costa, Afonso Duarte Leão de Souza. An antimicrobial diketopiperazine alkaloid and co-metabolites from an endophytic strain of Gliocladium isolated from Strychnos cf. toxifera. Natural product research. 2012 Nov; 26(21):2013-9. doi: 10.1080/14786419.2011.639070. [PMID: 22117164]
  • Ulrike Grienke, Judit Mihály-Bison, Daniela Schuster, Taras Afonyushkin, Markus Binder, Shu-hong Guan, Chun-ru Cheng, Gerhard Wolber, Hermann Stuppner, De-an Guo, Valery N Bochkov, Judith M Rollinger. Pharmacophore-based discovery of FXR-agonists. Part II: identification of bioactive triterpenes from Ganoderma lucidum. Bioorganic & medicinal chemistry. 2011 Nov; 19(22):6779-91. doi: 10.1016/j.bmc.2011.09.039. [PMID: 22014750]
  • K Cocquyt, P Cos, P Herdewijn, L Maes, P E Van den Steen, G Laekeman. Ajuga remota Benth.: from ethnopharmacology to phytomedical perspective in the treatment of malaria. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2011 Nov; 18(14):1229-37. doi: 10.1016/j.phymed.2011.08.063. [PMID: 22015320]
  • Ngan B Truong, Cuong V Pham, Huong T M Doan, Hung V Nguyen, Cuong M Nguyen, Hiep T Nguyen, Hong-jie Zhang, Harry H S Fong, Scott G Franzblau, Djaja D Soejarto, Minh V Chau. Antituberculosis cycloartane triterpenoids from Radermachera boniana. Journal of natural products. 2011 May; 74(5):1318-22. doi: 10.1021/np200022b. [PMID: 21469696]
  • Li-Shian Shi, Chih-Hua Chao, De-Yang Shen, Hsiu-Hui Chan, Chou-Hsiung Chen, Yu-Ren Liao, Shwu-Jen Wu, Yann-Lii Leu, Yuh-Chiang Shen, Yao-Haur Kuo, E-Jian Lee, Keduo Qian, Tian-Shung Wu, Kuo-Hsiung Lee. Biologically active constituents from the fruiting body of Taiwanofungus camphoratus. Bioorganic & medicinal chemistry. 2011 Jan; 19(1):677-83. doi: 10.1016/j.bmc.2010.10.032. [PMID: 21115251]
  • S Tewtrakul, P Tansakul, C Daengrot, C Ponglimanont, C Karalai. Anti-inflammatory principles from Heritiera littoralis bark. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2010 Sep; 17(11):851-5. doi: 10.1016/j.phymed.2010.02.011. [PMID: 20363114]
  • Daniel A Dias, Sylvia Urban. HPLC and NMR studies of phenoxazone alkaloids from Pycnoporus cinnabarinus. Natural product communications. 2009 Apr; 4(4):489-98. doi: . [PMID: 19475991]
  • Chao-Feng Zhang, Qiong Wang, Mian Zhang. [Studies on chemical constituents of Ligularia altaica]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 Apr; 32(4):524-6. doi: ". [PMID: 19645238]
  • Jeong Ah Kim, David Tay, Esperanza Carcache de Blanco. NF-kappaB inhibitory activity of compounds isolated from Cantharellus cibarius. Phytotherapy research : PTR. 2008 Aug; 22(8):1104-6. doi: 10.1002/ptr.2467. [PMID: 18570270]
  • Joo-Sang Lee, Chao-Mei Ma, Dong-Ki Park, Yasuharu Yoshimi, Minoru Hatanaka, Masao Hattori. Transformation of ergosterol peroxide to cytotoxic substances by rat intestinal bacteria. Biological & pharmaceutical bulletin. 2008 May; 31(5):949-54. doi: 10.1248/bpb.31.949. [PMID: 18451525]
  • Xiao-qi Zhang, Guo-liang Pang, Yan Cheng, Ying Wang, Wen-cai Ye. [Chemical constituents of the spores of Ganoderma lucidum]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2008 Jan; 31(1):41-4. doi: ". [PMID: 18589746]
  • Noélia Duarte, Maria-José U Ferreira, Marta Martins, Miguel Viveiros, Leonard Amaral. Antibacterial activity of ergosterol peroxide against Mycobacterium tuberculosis: dependence upon system and medium employed. Phytotherapy research : PTR. 2007 Jul; 21(7):601-4. doi: 10.1002/ptr.2119. [PMID: 17357175]
  • Francisco A Macías, Nuria Chinchilla, Rosa M Varela, José M G Molinillo. Bioactive steroids from Oryza sativa L. Steroids. 2006 Jul; 71(7):603-8. doi: 10.1016/j.steroids.2006.03.001. [PMID: 16620896]
  • Jian-fei Chao, Zhi-qi Yin, Wen-cai Ye, Shou-xun Zhao. [Chemical constituents from branch of Broussonetia papyrifera]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Jul; 31(13):1078-80. doi: ". [PMID: 17048607]
  • Sang Hyun Lee, Sang Hee Shim, Ju Sun Kim, Sam Sik Kang. Constituents from the fruiting bodies of Ganoderma applanatum and their aldose reductase inhibitory activity. Archives of pharmacal research. 2006 Jun; 29(6):479-83. doi: 10.1007/bf02969420. [PMID: 16833015]
  • Dong-Hyun Kim, Sung Je Jung, In-Sik Chung, Youn-Hyung Lee, Dae-Keun Kim, Sung-Hoon Kim, Byoung-Mog Kwon, Tae-Sook Jeong, Mi-Hyun Park, Nak-Sul Seoung, Nam-In Baek. Ergosterol peroxide from flowers of Erigeron annuus L. as an anti-atherosclerosis agent. Archives of pharmacal research. 2005 May; 28(5):541-5. doi: 10.1007/bf02977755. [PMID: 15974439]
  • Guo-Yu Li, Jin-Hui Wang, Xian Li. Sterols from the pericarp of Sphaerophysa salsula DC. Journal of Asian natural products research. 2005 Apr; 7(2):165-9. doi: 10.1080/10286020310001617192. [PMID: 15621621]
  • Li-Ming Yang Kuo, Kuei-Yuh Chen, Shy-Yuan Hwang, Jin-Liang Chen, Yen-Yin Liu, Chia-Ching Liaw, Po-Ho Ye, Cheng-Jen Chou, Chien-Chang Shen, Yao-Haur Kuo. DNA topoisomerase I inhibitor, ergosterol peroxide from Penicillium oxalicum. Planta medica. 2005 Jan; 71(1):77-9. doi: 10.1055/s-2005-837755. [PMID: 15678378]
  • K S Nam, Y S Jo, Y H Kim, J W Hyun, H W Kim. Cytotoxic activities of acetoxyscirpenediol and ergosterol peroxide from Paecilomyces tenuipes. Life sciences. 2001 Jun; 69(2):229-37. doi: 10.1016/s0024-3205(01)01125-0. [PMID: 11441913]
  • C L Cantrell, M S Rajab, S G Franzblau, F R Fronczek, N H Fischer. Antimycobacterial ergosterol-5,8-endoperoxide from Ajuga remota. Planta medica. 1999 Dec; 65(8):732-4. doi: 10.1055/s-1999-14053. [PMID: 10630115]